ES2355133T3 - Complejos de inclusión de butilftalida con derivados de ciclodextrina y procedimientos para su preparación. - Google Patents

Complejos de inclusión de butilftalida con derivados de ciclodextrina y procedimientos para su preparación. Download PDF

Info

Publication number: ES2355133T3
Authority: ES; Spain
Prior art keywords: butylphthalide; cyclodextrin; inclusion complex; cyclodextrin derivative; derivative
Prior art date: 2002-08-21
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

ES02760059T

Other languages

English (en)

Spanish (es)

Inventor

Zhan-Qi Niu

Kai Zhao

Wen-Juan Liu

Gui-Rong Zhou

Chao Liu

Rong-Duan Wang

Hong-Zhong Yuan

Wen-Min Guo

Sui-Chao Yan

Min Bai

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

SHIJIAZHUANG PHARMA GROUP ZHONGQI PHARMACEUTICALTECHNOLOGY (SHIJIAZHUANG) CO Ltd

Shijiazhuang Pharma Group Zhongqi Pharmaceutical Technology Co Ltd

Original Assignee

SHIJIAZHUANG PHARMA GROUP ZHONGQI PHARMACEUTICALTECHNOLOGY (SHIJIAZHUANG) CO Ltd

Shijiazhuang Pharma Group Zhongqi Pharmaceutical Technology Co Ltd

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2002-08-21

Filing date

2002-08-21

Publication date

2011-03-23

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=31892708&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=ES2355133(T3) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2002-08-21 Application filed by SHIJIAZHUANG PHARMA GROUP ZHONGQI PHARMACEUTICALTECHNOLOGY (SHIJIAZHUANG) CO Ltd, Shijiazhuang Pharma Group Zhongqi Pharmaceutical Technology Co Ltd filed Critical SHIJIAZHUANG PHARMA GROUP ZHONGQI PHARMACEUTICALTECHNOLOGY (SHIJIAZHUANG) CO Ltd

2011-03-23 Application granted granted Critical

2011-03-23 Publication of ES2355133T3 publication Critical patent/ES2355133T3/es

2022-08-21 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical class O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 title claims abstract description 67
238000000034 method Methods 0.000 title claims abstract description 25
238000002360 preparation method Methods 0.000 title claims abstract description 23
HJXMNVQARNZTEE-UHFFFAOYSA-N Butylphthalide Chemical compound C1=CC=C2C(CCCC)OC(=O)C2=C1 HJXMNVQARNZTEE-UHFFFAOYSA-N 0.000 claims abstract description 157
229950005197 butylphthalide Drugs 0.000 claims abstract description 78
ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 claims abstract description 34
229920000858 Cyclodextrin Polymers 0.000 claims abstract description 18
239000007787 solid Substances 0.000 claims abstract description 18
239000007788 liquid Substances 0.000 claims abstract description 17
239000000843 powder Substances 0.000 claims abstract description 8
238000001802 infusion Methods 0.000 claims abstract description 7
239000007924 injection Substances 0.000 claims abstract description 5
238000002347 injection Methods 0.000 claims abstract description 5
239000006188 syrup Substances 0.000 claims abstract description 3
235000020357 syrup Nutrition 0.000 claims abstract description 3
239000000243 solution Substances 0.000 claims description 32
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 26
239000000203 mixture Substances 0.000 claims description 19
PVPKHKNEWMXEIT-UHFFFAOYSA-N 3-butylbenzene-1,2-dicarboxamide Chemical compound CCCCC1=CC=CC(C(N)=O)=C1C(N)=O PVPKHKNEWMXEIT-UHFFFAOYSA-N 0.000 claims description 13
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
239000002904 solvent Substances 0.000 claims description 12
238000003756 stirring Methods 0.000 claims description 10
238000001035 drying Methods 0.000 claims description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 6
239000001116 FEMA 4028 Substances 0.000 claims description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 6
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 6
229960004853 betadex Drugs 0.000 claims description 6
238000001914 filtration Methods 0.000 claims description 5
239000004570 mortar (masonry) Substances 0.000 claims description 5
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
239000002552 dosage form Substances 0.000 claims description 4
PCWPQSDFNIFUPO-VDQKLNDWSA-N (1S,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21S,23R,25R,26S,28R,30R,31S,33R,35R,36R,37S,38R,39S,40R,41S,42R,43S,44R,45S,46R,47S,48R,49S)-37,39,41,43,45,47,49-heptakis(2-hydroxyethoxy)-5,10,15,20,25,30,35-heptakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontane-36,38,40,42,44,46,48-heptol Chemical compound OCCO[C@H]1[C@H](O)[C@@H]2O[C@H]3O[C@H](CO)[C@@H](O[C@H]4O[C@H](CO)[C@@H](O[C@H]5O[C@H](CO)[C@@H](O[C@H]6O[C@H](CO)[C@@H](O[C@H]7O[C@H](CO)[C@@H](O[C@H]8O[C@H](CO)[C@@H](O[C@H]1O[C@@H]2CO)[C@@H](O)[C@@H]8OCCO)[C@@H](O)[C@@H]7OCCO)[C@@H](O)[C@@H]6OCCO)[C@@H](O)[C@@H]5OCCO)[C@@H](O)[C@@H]4OCCO)[C@@H](O)[C@@H]3OCCO PCWPQSDFNIFUPO-VDQKLNDWSA-N 0.000 claims description 2
238000001816 cooling Methods 0.000 claims description 2
235000011187 glycerol Nutrition 0.000 claims description 2
238000002156 mixing Methods 0.000 claims description 2
239000002244 precipitate Substances 0.000 claims description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
238000003801 milling Methods 0.000 claims 1
239000012669 liquid formulation Substances 0.000 abstract description 4
239000003826 tablet Substances 0.000 abstract description 3
239000007919 dispersible tablet Substances 0.000 abstract description 2
239000008187 granular material Substances 0.000 abstract description 2
230000001225 therapeutic effect Effects 0.000 abstract description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 15
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 5
239000012153 distilled water Substances 0.000 description 5
239000008103 glucose Substances 0.000 description 5
239000007909 solid dosage form Substances 0.000 description 5
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 description 4
235000011175 beta-cyclodextrine Nutrition 0.000 description 4
241000283973 Oryctolagus cuniculus Species 0.000 description 3
230000007794 irritation Effects 0.000 description 3
208000028867 ischemia Diseases 0.000 description 3
239000008297 liquid dosage form Substances 0.000 description 3
239000011259 mixed solution Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
230000002792 vascular Effects 0.000 description 3
208000007536 Thrombosis Diseases 0.000 description 2
YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 2
239000002775 capsule Substances 0.000 description 2
201000010099 disease Diseases 0.000 description 2
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
238000009472 formulation Methods 0.000 description 2
238000007710 freezing Methods 0.000 description 2
230000008014 freezing Effects 0.000 description 2
229940093181 glucose injection Drugs 0.000 description 2
229940090044 injection Drugs 0.000 description 2
238000003760 magnetic stirring Methods 0.000 description 2
239000013642 negative control Substances 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
230000002265 prevention Effects 0.000 description 2
230000000699 topical effect Effects 0.000 description 2
210000003462 vein Anatomy 0.000 description 2
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
WGYGZQILDLRMMV-UHFFFAOYSA-N 2-n-butylbenzene-1,2-dicarboxamide Chemical compound CCCCNC(=O)C1=CC=CC=C1C(N)=O WGYGZQILDLRMMV-UHFFFAOYSA-N 0.000 description 1
208000030090 Acute Disease Diseases 0.000 description 1
206010020565 Hyperaemia Diseases 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
230000005856 abnormality Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
238000005054 agglomeration Methods 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
239000001387 apium graveolens Substances 0.000 description 1
229940114079 arachidonic acid Drugs 0.000 description 1
235000021342 arachidonic acid Nutrition 0.000 description 1
230000001746 atrial effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
-1 carboxymethyloxy cyclodextrin Chemical compound 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
230000009918 complex formation Effects 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
238000001599 direct drying Methods 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
238000001990 intravenous administration Methods 0.000 description 1
239000012528 membrane Substances 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
229940124531 pharmaceutical excipient Drugs 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229940127557 pharmaceutical product Drugs 0.000 description 1
239000011148 porous material Substances 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
238000001694 spray drying Methods 0.000 description 1
125000004963 sulfonylalkyl group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
230000008719 thickening Effects 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
230000003612 virological effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
- C08B37/0015—Inclusion compounds, i.e. host-guest compounds, e.g. polyrotaxanes
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/34—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide
- A61K31/343—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having five-membered rings with one oxygen as the only ring hetero atom, e.g. isosorbide condensed with a carbocyclic ring, e.g. coumaran, bufuralol, befunolol, clobenfurol, amiodarone
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
- A61K47/6951—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes using cyclodextrin
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Medicinal Chemistry (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
Epidemiology (AREA)
Nanotechnology (AREA)
Molecular Biology (AREA)
Medical Informatics (AREA)
Crystallography & Structural Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Polymers & Plastics (AREA)
Biophysics (AREA)
Biotechnology (AREA)
General Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Biochemistry (AREA)
General Chemical & Material Sciences (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Diabetes (AREA)
Hematology (AREA)
Medicinal Preparation (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)

ES02760059T 2002-08-21 2002-08-21 Complejos de inclusión de butilftalida con derivados de ciclodextrina y procedimientos para su preparación. Expired - Lifetime ES2355133T3 (es)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
PCT/CN2002/000579 WO2004018444A1 (fr)	2002-08-21	2002-08-21	Clathrates de phtalide butylique associe a de la cyclodextrine ou a ses derives, procede de preparation desdites compositions et leur utilisation

Publications (1)

Publication Number	Publication Date
ES2355133T3 true ES2355133T3 (es)	2011-03-23

Family

ID=31892708

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
ES02760059T Expired - Lifetime ES2355133T3 (es)	2002-08-21	2002-08-21	Complejos de inclusión de butilftalida con derivados de ciclodextrina y procedimientos para su preparación.

Country Status (12)

Country	Link
US (2)	US20060166931A1 (fr)
EP (1)	EP1535916B1 (fr)
JP (1)	JP4378755B2 (fr)
AT (1)	ATE489972T1 (fr)
AU (1)	AU2002327307B8 (fr)
BR (1)	BR0215848A (fr)
CA (1)	CA2494157C (fr)
DE (1)	DE60238510D1 (fr)
DK (1)	DK1535916T3 (fr)
ES (1)	ES2355133T3 (fr)
NO (1)	NO20050629L (fr)
WO (1)	WO2004018444A1 (fr)

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* Cited by examiner, † Cited by third party
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CN1605336A (zh)	2003-10-10	2005-04-13	中国医学科学院药物研究所	左旋丁基苯酞在制备预防和治疗脑梗塞的药物中的应用
CN1257711C (zh) *	2003-12-05	2006-05-31	石药集团中奇制药技术（石家庄）有限公司	丁苯酞软胶囊及其制备工艺
EP1757286B1 (fr)	2004-06-18	2017-09-06	CSPC Zhongqi Pharmaceutical Technology (Shijiazhuang) Co., Ltd.	Utilisation de l-n-butylphthalide pour la prevention ou le traitement de la maladie d'alzheimer
CN100361656C (zh) *	2004-08-27	2008-01-16	石药集团中奇制药技术（石家庄）有限公司	丁苯酞自乳化释药体系及其制备方法和应用
CN100367951C (zh)	2005-12-16	2008-02-13	石药集团恩必普药业有限公司	丁苯酞静脉乳剂及其应用
CN101342152B (zh) *	2007-07-10	2010-10-13	石药集团中奇制药技术（石家庄）有限公司	丁苯酞片及其制备方法
CN103505409B (zh) *	2012-06-27	2017-12-26	石药集团中奇制药技术（石家庄）有限公司	一种丁苯酞注射液及其制备方法
CN103784424B (zh) *	2012-10-30	2018-04-27	石药集团中奇制药技术（石家庄）有限公司	一种丁苯酞经皮贴剂及其制备方法
CN103127025B (zh) *	2013-03-06	2016-03-09	石家庄鸯星科技有限公司	消旋2-(α-羟基戊基)苯甲酸盐片的制备方法
CN105380908B (zh) *	2015-12-09	2018-08-10	河北大学	一种丁苯酞药物复合物及其制备方法和缓释制剂
CN108553412B (zh) *	2018-05-14	2019-10-29	田普森	一种含丁苯酞与增溶剂药物组合物
CN110548004B (zh) *	2018-05-30	2023-05-16	成都施贝康生物医药科技有限公司	一种稳定的丁苯酞大容量注射液及其制备方法
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CN114685410B (zh) *	2020-12-26	2023-09-29	四川汇宇制药股份有限公司	一种丁苯酞的制备方法
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2002
- 2002-08-21 DK DK02760059.2T patent/DK1535916T3/da active
- 2002-08-21 AT AT02760059T patent/ATE489972T1/de active
- 2002-08-21 AU AU2002327307A patent/AU2002327307B8/en not_active Expired
- 2002-08-21 EP EP02760059A patent/EP1535916B1/fr not_active Expired - Lifetime
- 2002-08-21 CA CA2494157A patent/CA2494157C/fr not_active Expired - Lifetime
- 2002-08-21 BR BR0215848-5A patent/BR0215848A/pt not_active Application Discontinuation
- 2002-08-21 ES ES02760059T patent/ES2355133T3/es not_active Expired - Lifetime
- 2002-08-21 WO PCT/CN2002/000579 patent/WO2004018444A1/fr not_active Ceased
- 2002-08-21 JP JP2004529646A patent/JP4378755B2/ja not_active Expired - Lifetime
- 2002-08-21 US US10/524,653 patent/US20060166931A1/en not_active Abandoned
- 2002-08-21 DE DE60238510T patent/DE60238510D1/de not_active Expired - Lifetime
2005
- 2005-02-04 NO NO20050629A patent/NO20050629L/no not_active Application Discontinuation
2008
- 2008-08-28 US US12/200,130 patent/US7678776B2/en not_active Expired - Lifetime

Also Published As

Publication number	Publication date
HK1074200A1 (en)	2005-11-04
JP2006500367A (ja)	2006-01-05
DK1535916T3 (da)	2011-03-14
EP1535916A1 (fr)	2005-06-01
CA2494157C (fr)	2010-10-12
AU2002327307A1 (en)	2004-03-11
CA2494157A1 (fr)	2004-03-04
AU2002327307B2 (en)	2009-02-12
WO2004018444A1 (fr)	2004-03-04
JP4378755B2 (ja)	2009-12-09
US7678776B2 (en)	2010-03-16
US20080318898A1 (en)	2008-12-25
EP1535916B1 (fr)	2010-12-01
ATE489972T1 (de)	2010-12-15
EP1535916A4 (fr)	2006-09-20
US20060166931A1 (en)	2006-07-27
AU2002327307B8 (en)	2009-02-26
NO20050629L (no)	2005-03-17
DE60238510D1 (de)	2011-01-13
BR0215848A (pt)	2005-06-21

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